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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2320.
Published online 2009 September 5. doi:  10.1107/S1600536809034138
PMCID: PMC2970361

1-Allyl-3-chloro-6-nitro-1H-indazole

Abstract

The indazole system in each of the two independent mol­ecules of the title compound, C10H8ClN3O2, is planar (r.m.s. deviations = 0.005 and 0.005 Å). The nitro group is coplanar with the fused-ring system [dihedral angles = 1.3 (3) and 4.8 (3) Å].

Related literature

For a review of indazoles, see: Elguéro (1996 [triangle]); Elguéro et al. (1995 [triangle]).

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Object name is e-65-o2320-scheme1.jpg

Experimental

Crystal data

  • C10H8ClN3O2
  • M r = 237.64
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2320-efi1.jpg
  • a = 7.6804 (1) Å
  • b = 9.9559 (2) Å
  • c = 28.4344 (4) Å
  • β = 95.144 (1)°
  • V = 2165.49 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.34 mm−1
  • T = 295 K
  • 0.4 × 0.3 × 0.2 mm

Data collection

  • Bruker APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.884, T max = 0.934
  • 19833 measured reflections
  • 3777 independent reflections
  • 2665 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.185
  • S = 1.07
  • 3777 reflections
  • 289 parameters
  • H-atom parameters constrained
  • Δρmax = 0.78 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034138/tk2531sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034138/tk2531Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

3-Chloro-6-nitroindazole (5 mmol) and allyl bromide (10 mmol) were reacted in THF (40 ml) in the presence of potassium carbonate (10 mmol) and tetra-n-butylammonium bromide (0.5 mmol). The mixture was stirred for 24 h, filtered, and the THF removed under vacuum. The product was separated by chromatography on silica gel with a hexane:ethyl acetate (9:1) solvent system. The compound was obtained as yellow crystals in 50% yield; m.p. 351 K.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.97 Å) and were included in the refinement in the riding model approximation with U(H) set to 1.2U(C).

Although data were measured to a high 2θ limit, those reflections beyond 50 ° were not used as their inclusion significantly raised the R index.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C10H8ClN3O2 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C10H8ClN3O2F(000) = 976
Mr = 237.64Dx = 1.458 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6549 reflections
a = 7.6804 (1) Åθ = 2.2–29.5°
b = 9.9559 (2) ŵ = 0.34 mm1
c = 28.4344 (4) ÅT = 295 K
β = 95.144 (1)°Prism, yellow
V = 2165.49 (6) Å30.4 × 0.3 × 0.2 mm
Z = 8

Data collection

Bruker APEX2 diffractometer3777 independent reflections
Radiation source: fine-focus sealed tube2665 reflections with I > 2σ(I)
graphiteRint = 0.032
[var phi] and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.884, Tmax = 0.934k = −11→11
19833 measured reflectionsl = −33→33

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.1031P)2 + 0.7179P] where P = (Fo2 + 2Fc2)/3
3777 reflections(Δ/σ)max = 0.001
289 parametersΔρmax = 0.78 e Å3
0 restraintsΔρmin = −0.29 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl10.30814 (12)0.06578 (10)0.03474 (3)0.0718 (3)
Cl20.94159 (18)0.35838 (12)0.02733 (4)0.0958 (4)
O10.6481 (4)0.0762 (3)0.28950 (9)0.0866 (9)
O20.7296 (4)0.2788 (3)0.27899 (9)0.0867 (9)
O31.2186 (4)0.2329 (4)0.28256 (10)0.1089 (11)
O41.0809 (4)0.0460 (3)0.27538 (10)0.0928 (9)
N10.5287 (3)0.3527 (3)0.10386 (9)0.0563 (7)
N20.4505 (4)0.2960 (3)0.06380 (9)0.0606 (8)
N30.6601 (4)0.1750 (3)0.26458 (9)0.0582 (7)
N40.8630 (3)0.0501 (3)0.09910 (10)0.0529 (7)
N50.8504 (4)0.1220 (3)0.05846 (10)0.0622 (8)
N61.1300 (4)0.1509 (4)0.25934 (11)0.0659 (8)
C10.4072 (4)0.1742 (4)0.07565 (11)0.0523 (8)
C20.4547 (3)0.1450 (3)0.12352 (11)0.0451 (7)
C30.4413 (4)0.0352 (3)0.15351 (11)0.0509 (8)
H30.3882−0.04410.14240.061*
C40.5079 (4)0.0470 (3)0.19951 (11)0.0510 (8)
H40.5003−0.02440.22030.061*
C50.5876 (4)0.1675 (3)0.21511 (10)0.0458 (7)
C60.6039 (4)0.2781 (3)0.18747 (10)0.0447 (7)
H60.65700.35680.19910.054*
C70.5353 (4)0.2648 (3)0.14059 (11)0.0447 (7)
C80.6026 (5)0.4877 (4)0.10227 (14)0.0678 (10)
H8A0.67370.50390.13170.081*
H8B0.67930.49090.07700.081*
C90.4777 (6)0.5939 (5)0.0952 (2)0.0994 (15)
H90.40340.60410.11910.119*
C100.4537 (7)0.6752 (5)0.0618 (2)0.1091 (18)
H10A0.52320.67100.03660.131*
H10B0.36630.73980.06200.131*
C110.9279 (4)0.2371 (4)0.06933 (11)0.0588 (9)
C120.9941 (4)0.2448 (3)0.11660 (11)0.0488 (8)
C131.0839 (4)0.3397 (3)0.14605 (13)0.0563 (8)
H131.11300.42320.13430.068*
C141.1278 (4)0.3072 (4)0.19233 (13)0.0563 (9)
H141.18850.36810.21240.068*
C151.0808 (4)0.1816 (3)0.20921 (11)0.0491 (8)
C160.9938 (3)0.0852 (3)0.18217 (11)0.0453 (7)
H160.96510.00230.19440.054*
C170.9510 (3)0.1194 (3)0.13522 (11)0.0435 (7)
C180.8035 (4)−0.0888 (3)0.09845 (13)0.0615 (9)
H18A0.6969−0.09630.07760.074*
H18B0.7766−0.11420.12990.074*
C190.9352 (5)−0.1820 (4)0.08251 (14)0.0701 (10)
H190.9748−0.16580.05310.084*
C200.9988 (6)−0.2813 (5)0.1052 (2)0.1019 (16)
H20A0.9629−0.30120.13480.122*
H20B1.0817−0.33500.09240.122*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0785 (6)0.0739 (7)0.0602 (6)−0.0018 (5)−0.0089 (4)−0.0182 (4)
Cl20.1491 (11)0.0756 (9)0.0649 (6)0.0153 (7)0.0215 (6)0.0187 (5)
O10.128 (2)0.072 (2)0.0577 (15)0.0029 (16)−0.0050 (15)0.0184 (15)
O20.116 (2)0.081 (2)0.0593 (16)−0.0218 (17)−0.0108 (15)−0.0064 (14)
O30.126 (2)0.121 (3)0.0733 (19)−0.021 (2)−0.0282 (18)−0.0127 (19)
O40.133 (3)0.074 (2)0.0688 (18)0.0066 (18)−0.0030 (16)0.0176 (16)
N10.0649 (16)0.0493 (18)0.0536 (16)−0.0039 (13)−0.0018 (12)0.0018 (13)
N20.0677 (16)0.063 (2)0.0494 (16)0.0022 (14)−0.0031 (13)−0.0010 (14)
N30.0651 (16)0.060 (2)0.0495 (16)0.0074 (14)0.0058 (13)−0.0029 (15)
N40.0516 (14)0.0464 (18)0.0606 (17)0.0000 (12)0.0055 (12)−0.0086 (13)
N50.0684 (17)0.062 (2)0.0560 (17)0.0127 (15)0.0025 (13)−0.0061 (15)
N60.0645 (17)0.071 (2)0.0614 (19)0.0134 (16)−0.0007 (15)−0.0084 (18)
C10.0503 (16)0.053 (2)0.0530 (19)0.0056 (14)0.0033 (14)−0.0088 (16)
C20.0388 (14)0.043 (2)0.0543 (18)0.0061 (12)0.0063 (13)−0.0087 (14)
C30.0506 (16)0.041 (2)0.062 (2)0.0009 (13)0.0101 (14)−0.0064 (16)
C40.0567 (17)0.042 (2)0.0556 (19)0.0068 (14)0.0119 (15)0.0031 (15)
C50.0443 (15)0.047 (2)0.0469 (17)0.0094 (13)0.0072 (13)−0.0022 (14)
C60.0449 (15)0.0386 (19)0.0504 (17)0.0050 (12)0.0027 (13)−0.0055 (14)
C70.0414 (14)0.0427 (19)0.0503 (17)0.0079 (13)0.0066 (12)−0.0006 (15)
C80.078 (2)0.054 (2)0.069 (2)−0.0089 (19)−0.0050 (18)0.0130 (18)
C90.085 (3)0.078 (3)0.134 (4)−0.011 (2)0.000 (3)0.021 (3)
C100.108 (3)0.080 (4)0.132 (4)−0.019 (3)−0.023 (3)0.046 (3)
C110.072 (2)0.050 (2)0.055 (2)0.0154 (17)0.0094 (17)0.0019 (16)
C120.0496 (16)0.040 (2)0.0581 (18)0.0094 (13)0.0139 (14)−0.0024 (15)
C130.0630 (19)0.036 (2)0.072 (2)−0.0020 (14)0.0176 (17)−0.0019 (16)
C140.0510 (16)0.047 (2)0.072 (2)−0.0019 (14)0.0107 (15)−0.0194 (17)
C150.0446 (15)0.045 (2)0.0577 (19)0.0105 (13)0.0057 (14)−0.0034 (15)
C160.0460 (15)0.0322 (18)0.0589 (18)0.0040 (12)0.0105 (13)0.0000 (14)
C170.0389 (14)0.0354 (18)0.0567 (18)0.0060 (12)0.0075 (13)−0.0060 (14)
C180.0579 (18)0.050 (2)0.077 (2)−0.0065 (15)0.0049 (16)−0.0166 (18)
C190.085 (2)0.056 (3)0.072 (2)0.001 (2)0.0204 (19)−0.002 (2)
C200.096 (3)0.082 (4)0.131 (4)0.013 (3)0.030 (3)0.027 (3)

Geometric parameters (Å, °)

Cl1—C11.714 (3)C6—H60.9300
Cl2—C111.708 (4)C8—C91.430 (6)
O1—N31.221 (4)C8—H8A0.9700
O2—N31.218 (4)C8—H8B0.9700
O3—N61.219 (4)C9—C101.250 (6)
O4—N61.213 (4)C9—H90.9300
N1—C71.360 (4)C10—H10A0.9300
N1—N21.362 (4)C10—H10B0.9300
N1—C81.461 (4)C11—C121.396 (4)
N2—C11.309 (5)C12—C131.402 (5)
N3—C51.468 (4)C12—C171.408 (4)
N4—N51.356 (4)C13—C141.368 (5)
N4—C171.365 (4)C13—H130.9300
N4—C181.456 (4)C14—C151.398 (5)
N5—C111.316 (5)C14—H140.9300
N6—C151.474 (4)C15—C161.367 (4)
C1—C21.408 (4)C16—C171.388 (4)
C2—C31.396 (4)C16—H160.9300
C2—C71.410 (4)C18—C191.474 (5)
C3—C41.366 (4)C18—H18A0.9700
C3—H30.9300C18—H18B0.9700
C4—C51.401 (4)C19—C201.255 (6)
C4—H40.9300C19—H190.9300
C5—C61.365 (4)C20—H20A0.9300
C6—C71.395 (4)C20—H20B0.9300
C7—N1—N2111.0 (3)H8A—C8—H8B107.5
C7—N1—C8128.9 (3)C10—C9—C8129.6 (6)
N2—N1—C8119.9 (3)C10—C9—H9115.2
C1—N2—N1105.8 (3)C8—C9—H9115.2
O2—N3—O1122.8 (3)C9—C10—H10A120.0
O2—N3—C5118.9 (3)C9—C10—H10B120.0
O1—N3—C5118.3 (3)H10A—C10—H10B120.0
N5—N4—C17111.6 (3)N5—C11—C12113.1 (3)
N5—N4—C18119.5 (3)N5—C11—Cl2120.4 (3)
C17—N4—C18128.6 (3)C12—C11—Cl2126.5 (3)
C11—N5—N4105.3 (3)C11—C12—C13136.8 (3)
O4—N6—O3123.4 (4)C11—C12—C17103.6 (3)
O4—N6—C15118.8 (3)C13—C12—C17119.5 (3)
O3—N6—C15117.8 (4)C14—C13—C12118.7 (3)
N2—C1—C2113.0 (3)C14—C13—H13120.6
N2—C1—Cl1121.1 (3)C12—C13—H13120.6
C2—C1—Cl1125.9 (3)C13—C14—C15119.6 (3)
C3—C2—C1136.5 (3)C13—C14—H14120.2
C3—C2—C7120.4 (3)C15—C14—H14120.2
C1—C2—C7103.1 (3)C16—C15—C14124.3 (3)
C4—C3—C2118.4 (3)C16—C15—N6117.9 (3)
C4—C3—H3120.8C14—C15—N6117.8 (3)
C2—C3—H3120.8C15—C16—C17115.5 (3)
C3—C4—C5119.5 (3)C15—C16—H16122.2
C3—C4—H4120.3C17—C16—H16122.2
C5—C4—H4120.3N4—C17—C16131.2 (3)
C6—C5—C4124.7 (3)N4—C17—C12106.4 (3)
C6—C5—N3117.7 (3)C16—C17—C12122.4 (3)
C4—C5—N3117.7 (3)N4—C18—C19112.2 (3)
C5—C6—C7115.3 (3)N4—C18—H18A109.2
C5—C6—H6122.4C19—C18—H18A109.2
C7—C6—H6122.4N4—C18—H18B109.2
N1—C7—C6131.1 (3)C19—C18—H18B109.2
N1—C7—C2107.2 (3)H18A—C18—H18B107.9
C6—C7—C2121.8 (3)C20—C19—C18125.7 (4)
C9—C8—N1115.3 (3)C20—C19—H19117.1
C9—C8—H8A108.5C18—C19—H19117.1
N1—C8—H8A108.5C19—C20—H20A120.0
C9—C8—H8B108.5C19—C20—H20B120.0
N1—C8—H8B108.5H20A—C20—H20B120.0
C7—N1—N2—C10.7 (3)N2—N1—C8—C970.4 (5)
C8—N1—N2—C1176.4 (3)N1—C8—C9—C10−116.9 (5)
C17—N4—N5—C11−1.0 (3)N4—N5—C11—C120.3 (4)
C18—N4—N5—C11−174.4 (3)N4—N5—C11—Cl2179.8 (2)
N1—N2—C1—C2−0.2 (4)N5—C11—C12—C13−179.6 (3)
N1—N2—C1—Cl1−178.6 (2)Cl2—C11—C12—C130.9 (6)
N2—C1—C2—C3−179.7 (3)N5—C11—C12—C170.4 (3)
Cl1—C1—C2—C3−1.4 (5)Cl2—C11—C12—C17−179.0 (2)
N2—C1—C2—C7−0.3 (3)C11—C12—C13—C14−179.7 (3)
Cl1—C1—C2—C7178.1 (2)C17—C12—C13—C140.2 (4)
C1—C2—C3—C4179.3 (3)C12—C13—C14—C15−0.7 (4)
C7—C2—C3—C40.0 (4)C13—C14—C15—C160.9 (5)
C2—C3—C4—C5−0.3 (4)C13—C14—C15—N6−179.7 (3)
C3—C4—C5—C60.5 (4)O4—N6—C15—C16−5.2 (4)
C3—C4—C5—N3−179.0 (3)O3—N6—C15—C16174.8 (3)
O2—N3—C5—C60.7 (4)O4—N6—C15—C14175.4 (3)
O1—N3—C5—C6−179.1 (3)O3—N6—C15—C14−4.6 (4)
O2—N3—C5—C4−179.8 (3)C14—C15—C16—C17−0.5 (4)
O1—N3—C5—C40.4 (4)N6—C15—C16—C17−179.9 (2)
C4—C5—C6—C7−0.5 (4)N5—N4—C17—C16−180.0 (3)
N3—C5—C6—C7179.0 (2)C18—N4—C17—C16−7.3 (5)
N2—N1—C7—C6179.3 (3)N5—N4—C17—C121.3 (3)
C8—N1—C7—C64.0 (5)C18—N4—C17—C12174.0 (3)
N2—N1—C7—C2−0.8 (3)C15—C16—C17—N4−178.6 (3)
C8—N1—C7—C2−176.1 (3)C15—C16—C17—C120.0 (4)
C5—C6—C7—N1−180.0 (3)C11—C12—C17—N4−1.0 (3)
C5—C6—C7—C20.2 (4)C13—C12—C17—N4179.0 (3)
C3—C2—C7—N1−179.8 (3)C11—C12—C17—C16−179.9 (3)
C1—C2—C7—N10.7 (3)C13—C12—C17—C160.2 (4)
C3—C2—C7—C60.1 (4)N5—N4—C18—C1981.6 (4)
C1—C2—C7—C6−179.5 (3)C17—N4—C18—C19−90.5 (4)
C7—N1—C8—C9−114.7 (4)N4—C18—C19—C20123.4 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2531).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Elguéro, J. (1996). Comprehensive Heterocyclic Chemistry II, edited by I. Shinkai, Vol. 3, p. 1. Oxford: Elsevier Science.
  • Elguéro, J., Fruchier, A., Tjiou, E. M. & Trofimenko, S. (1995). Chem. Heterocycl. Compd (Engl. Transl.), 31, 1006–1026.
  • Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography